Rangers crashed out of the Scottish League Cup 2-1 after extra-time at Forfar - hours after Charles Green warned boss Ally McCoist he must win a cup this season.
Former chief executive Green, who is to return to Ibrox as a consultant, told a newspaper earlier on Saturday that simply winning the league will not be enough for the Light Blues.
But the Glasgow side failed even to overcome the first hurdle in the League Cup as their fellow League 1 rivals came out on top at Station Park.
Rangers headed into the match on the back of fresh off-field turmoil as a result of a bitter boardroom battle, in which a group of shareholders seek the removal of key board members, and the action on the park did not offer much comfort for fans either.
Gavin Swankie handed the home side an early opener, which was cancelled out by Fraser Aird, before Swankie netted again deep into extra-time.
Andy Mitchell, Chris Hegarty and David Templeton were added to the Gers side following last week's Ramsdens Cup win over Albion Rovers, with new recruits Nicky Law and Jon Daly ineligible and Kyle McAusland dropping to the bench.
A transfer embargo means Rangers are unable to register any of their eight new signings until September 1 and the cup rules state they cannot feature as trialists in this competition.
Andy Little was tasked with leading the line for Rangers, with Lee McCulloch shoring up the defence in the absence of the injured Emilson Cribari.
Forfar were up for the match right from the outset and a low drive from Gavin Malin was comfortably gathered by Scott Gallacher.
The home side surged into the lead when a communication mix-up between Gallacher and McCulloch allowed Swankie to pounce and lob the goalkeeper to claim the opener after just eight minutes.